Ethyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-oxazole-4-carboxylate → Ethyl cis(+/-)-2-(4-amino-3-methoxypiperidin-1-yl)-1,3-oxazole-4-carboxylate

HRID 43603Notes

Reaction equation

HRID 43603 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[O:19][CH:20]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:22]=2)[CH2:14][C@H:13]1[O:28][CH3:29])=O)C1C=CC=CC=1>[Pd].C(O)C>[NH2:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[O:19][CH:20]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:22]=2)[CH2:14][C@H:13]1[O:28][CH3:29]

Participants

4

Reactant 1

HCID 86648578Ethyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-oxazole-4-carboxylate

Product 1

HCID 86648577Ethyl cis(+/-)-2-(4-amino-3-methoxypiperidin-1-yl)-1,3-oxazole-4-carboxylateYield 102.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The same operation as in Example (95b) was performed using ethyl cis(±)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-oxazole-4-carboxylate obtained in Example (103c) (0.7 g, 1.74 mmol), 10% Pd/C (0.25 g) and ethanol (10 mL), to obtain 0.48 g of the title compound as a yellow amorphous solid (100%).

Sources & evidence

ORD record
ord-40682ac7abc54d46ac292e92bcf2851f
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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